Issue 2, 2015

Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides

Abstract

Stereoselective synthesis of pyrazolidinones via dipolar cycloaddition of azomethine imines with active esters under Lewis base catalysis is presented. The active esters are readily generated in situ from the corresponding acids. Products, which are obtained with excellent diastereocontrol and high enantioselectivity, contain along with the pyrazolidinone core also the tetrahydroisoquinoline structural motif. Theoretical studies give insight into the mechanism of the formal cycloaddition reaction.

Graphical abstract: Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides

Supplementary files

Article information

Article type
Edge Article
Submitted
27 Aug 2014
Accepted
14 Nov 2014
First published
19 Nov 2014
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2015,6, 1252-1257

Author version available

Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides

L. Hesping, A. Biswas, C. G. Daniliuc, C. Mück-Lichtenfeld and A. Studer, Chem. Sci., 2015, 6, 1252 DOI: 10.1039/C4SC02612H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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